


Let's play the pronoun game!

by zation



Category: Supernatural
Genre: Alternate Universe - High School, Alternate Universe - Modern Setting, Anal Sex, Blow Jobs, Boys in Skirts, Cas wants it too, Cheerleader Castiel, Cheerleaders, Confused Dean, Confusion, Crossdressing, Crossdressing Castiel, Cute Castiel, Dean Has a Crush, Dean likes Cas in skirts, Dean really has no clue at first, Dean the knight in shining armor, Dean tries to be proper but really wants sex with Cas, Everyone is very accepting, Explicit Sexual Content, First Time, Fluff, Gender Bender, Gender Confusion, Hand Jobs, Humor, Inappropriate Erections, Lots of Sex, M/M, Misunderstandings, Mostly porn, Oblivious Dean, Panty Kink, Porn With Plot, Protective Dean, Semi-Public Sex, Sex in the Impala, Sexual discoveries, Shameless Smut, Skirt Kink, We're only having fun over here, crackfic, extremely little plot
Language: English
Status: Completed
Published: 2016-06-02
Updated: 2016-06-09
Packaged: 2018-07-11 18:18:57
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 2
Words: 17,907
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/7064932
Author URL: https://archiveofourown.org/users/zation/pseuds/zation
Summary: <blockquote class="userstuff">
              <p>When Dean first lays his eyes on Cas he immediately thinks she’s the most beautiful girl he’s ever seen. New to the school and to town, Dean sets out on a determined path to stumblingly woo this beautiful apparition.</p><p>Or, </p><p>The one where cross-dressing Castiel gets a love-sick, somewhat confused puppy on his trail.</p>
            </blockquote>





	1. In which Dean is in for a surprise

**Author's Note:**

  * Translation into Español available: [¡Vamos a jugar el juego del pronombre! (Traducción)](https://archiveofourown.org/works/11424033) by [Kainsami](https://archiveofourown.org/users/Kainsami/pseuds/Kainsami)

**Summary for the Chapter:**

> Silly silliness

**Notes for the Chapter:**

> My first real cross-dressing fic, I’m so nervous! Thank you for reading and I hope you’ll have as much fun as I had writing it! Fumbling Dean is the best <3
> 
> EDIT: Now beta read by my darling BeeCas who totally works too hard! Love you, honey!
> 
> EDIT 2: Please note the translation into Spanish, I'm so happy and proud! Thank you, Kain!

  
  


Dean was actually kind of enjoying this new school. It was his senior year of high school so he supposed he ought to enjoy it but it wasn’t just that.

First of all, it was big. Like, humongous. The main building could have easily fitted his old high school times two. And while the size of the buildings (that’s right, there was more than one) didn’t particularly matter it was rather the size of the student body that impressed Dean. It was about thrice as big as his old one and that ensured totally anonymity, even for the new kids. And that was awesome.

Dad had moved them here just three weeks prior and had told them that yes, this would be the one that stuck. Life had been wobbly there for a while, what with mom dying and shit hitting the fan, but apparently dad had decided that now that Sammy was entering high school too, well _now_ they kind of had to settle down. Dean wasn’t even bitter his high school years had been spent school hopping, not as long as they stayed still now.

Wasn’t like he was going to go to college anyway. Or maybe he could actually go to State now? Possibilities started seeming endless as soon as they became stationary.

Also, the food in this school’s cafeteria was the bomb. Better than home cooked (not surprisingly since Dean was the one cooking at home).

Another good thing about this school was that people seemed friendly. He and Sammy had been kind of sticking to the house for those first two weeks in town but now, after only barely a week of school, they had both managed to get some friends. Dean supposed it helped that he and Sam weren’t the only new kids, not in a school this big. Was nice, not being the token oddball.

But the best thing, the indisputably, super best thing of everything? Well that was the cheerleaders.

Dad had given Dean the Impala so he could drive to school instead of him and Sammy having to rely on the bus but already on the second day of school dad’s truck had kind of broken down and he had ended up using the Impala for two days. Dean had grumbled while Sam had sighed and they had ended up walking to school, bus be fucking damned.

As it turned out, if they took a shortcut through the woods they ended up behind the football field and that ended up shorter than waiting for the school bus. Weird but true.

Anyway, Dean had stopped grumbling the second his eyes landed on the football field. Because there the cheerleaders were. Already in full practice mode, the team they were supposedly cheering for nowhere to be seen but fuck if Dean cared.

All he saw were long legs, flapping skirts, rustling pompoms, and swishing pony tails. Perfection.

There were some guys on the team as well and they did a really fucking good job of throwing the girls in the air, catching them in intimate embraces on their way down. Fuck Dean’s fucking luck for not being born an athlete.

So Dean might have gone back to that field only to notice that the cheerleaders seemed to be practicing almost every morning and who could fucking blame him for lingering? Jesus, they were like works of art.

Dean had always loved all kinds of women, short and tall, flat and curvy, long-haired and short-haired. Dean just loved women. And oh boy, the cheerleaders were something else.

Dean didn’t even like football and yet he found himself extremely inspired as soon as the girls started waving their pompoms around. Some stood out more than others, of course.

There was a redhead with a strong voice.

_Imagine her screaming my name in ecstasy._

There was a blonde with a smile so cheeky he could see it from the bleachers.

_Imagine the way she would challenge me._

There was a brunette with a thick ponytail.

_Imagine running my fingers through that._

But all of them paled in comparison to this one particular girl.

She had hair so dark brown it almost looked black, it was cut in a boyish style, not nearly as short as Dean’s standard cut but definitely shorter than her friends. It suited her perfectly.

She carried herself with such dignity that it left Dean awed. He couldn’t see much details from how far away he usually was but he had been able to tell that her features were fine and sharp. And God, she just flew through the air as if she was born to do it.

Yeah, just about a week into the new school year, new school and everything, and Dean was already reduced to a gawking mess. This was going to be a _fun_ year.

  


*****

  


Week number two started swimmingly. That was to say, it didn’t start swimmingly at all.

Sam had convinced Dean to start taking AP Math because apparently Dean was smart or something. This was all news to him but Sammy had been thoroughly unimpressed with Dean’s arguments. Plus, if he did really good he could maybe get into State after all. And maybe he wanted that now, he wasn’t so sure.

So instead of dilly-dallying about whether or not it was worth taking AP Math because he might or might not even apply for any colleges on which applications this particular class would look good, he just up and went with it.

Problem was, he had barely learned where all his other classes were and now he was suddenly overcome with the problem of finding this new one.

The map the student counselor had given him was of course useless but that was nothing new.

Nevertheless he had his eyes glued to it as he rounded a corner (probably the wrong corner) which was why he ended up smacking right into the girl coming from the other way.

She yelped and ended up on her rump, her books scattered between them and Dean was just staring like a goddamn moron. Because, of fucking course, out of everyone he could have bumped into and sent sprawling it had to be the sexy-as-sin cheerleader.

"Sorry." He stuttered (fucking stuttered!) and immediately sat down to help her gather her books.

Fucking shit, she still had her cheerleading outfit on. The skirt had risen when she sat down and showed off a creamy white thigh. Dean had to tear his eyes away.

"Thank you." She said when he handed her the books and just goddamn…

Her voice was a little deeper than most girls but it was rich in a pleasant way, sent fucking shivers down Dean’s spine and whatever. And God, her _eyes_.

So, okay, sure. Dean _was_ a teenager but he wasn’t a blubbering fool. Usually.

The way he just kind of stared as the girl got to her feet would perhaps argue against that statement. Shit, he shot to his feet in the last second and realized too late what a great opportunity he had just missed. Should’ve offered his hand to help her up and then masturbate with that hand. No! Jesus, just fucking help her, nothing else.

Dean was a fucking mess.

"Are you new?"

_Fucking concentrate, Winchester._

He looked down when he saw that she was pointing to the map he was still clutching (like a doofus).

"Yeah." He all but squeaked. Fucking puberty making his fucking voice crack. "I was just, you know, trying to find room A11, but…" he trailed off when she smiled a goddamn fucking dazzling smile at him. What the fuck was going on?!

"Me too." She said cheerily. "I’ll walk you."

"You’re in senior AP Math?" he cleared his throat when she tilted her head to the side questioningly. "I-I mean, not that you couldn’t be… I was more like, what are the odds, you know?"

She smiled again, smaller and more secretive. Were Dean’s knees shaking?

"I’m Cas." She held out her hand for him to shake.

Dean’s knees were shaking.

"I’m Dean."

Her grip was firm and her palm smooth.

_Don’t think about where you’re gonna put that hand later. Just don’t go there. Don’t._

"Welcome to our school, Dean." Cas smiled.

_Fucking don’t! What the fuck’s wrong with you?!_

"Thanks." He mumbled and immediately started following Cas when she indicated that they needed to go.

"So, have you been in town long?"

How the fuck Dean managed to fumble and mumble himself through a whole conversation he would never know. But Cas was just so attentive. Listened so well to Dean when he told her about his dad getting a job here, about Sammy, and about the school in general. Listened and asked the right questions and Jesus Christ, it was hard to concentrate with her this up close.

Her hair was pulled back from her face by a thin headband and it curled nicely around her neck. It was short enough that it barely grazed her shoulders but looked so thick and shiny that Dean’s hands were practically shaking from the need to touch it.

Her blue eyes tracked Dean’s every movement and God, she looked at him as if she needed to memorize his every feature. Dean had never felt so seen.

She had a lithe build, which he already knew from what he had seen during practice but shit, seeing her move so up close was like a dream. She was just so… so smooth in her movements.

The skirt swished around her thighs and he tried really hard not to stare. It wasn’t like this was his first fucking time seeing a girl in a skirt for God’s sake. And he wasn’t a blushing virgin either so what the fuck?

But she smelled so good and looked so supple and just _nngh_ …

She had a rather flat chest but Dean didn’t mind, not at fucking all. It suited her perfectly, made her whole visage proportionate and yeah, Dean was sweating by the time they reached the classroom.

"Here we are." Cas said cheerily and Dean smiled shakily.

As soon as they entered the classroom Cas’ friends called out to her. Dean immediately recognized the two girls as the blonde and the brunette from the cheerleading squad, and not just because they had their cheerleading outfits on as well. Man, they were pretty but Cas… Cas was…

Dean had to turn his head away so he wouldn’t get caught staring at her butt as she walked over to her friends.

And he had to talk to the teacher before class so he ended up sitting in the only seat left, which was just in front of the teacher’s desk but he didn’t mind.

This way he could spend the class imagining that Cas and her friends were looking at his back, tittering about him.

Best part was when he accidentally (he pushed it) dropped his pen over the edge of the desk and had to lean down to retrieve it. The angle made it easy for him to glance in Cas’ direction and to his immense pleasure he found her looking openly at him.

He winked at her and she smiled prettily back.

Dean came with a shout in the shower that evening. Sam’s bitchface was almost better than the actual orgasm.

  


*****

  


AP Math quickly became Dean’s favorite class. Not because he and Cas actually spent it talking all that much but because Cas was in it. Simply just there.

Dean had stopped stalking the football field, figuring he very well couldn’t be there for every cheerleading practice or it would look weird. He would either be labelled stalker or pathetic puppy and while that maybe wasn’t so wrong he’d rather avoid it.

Lord knew he tried other stuff, though.

He had befriended Benny, a cool guy with a southern drawl that Dean teased him for but secretly kind of thought was cool (and hot. Maybe?). With Benny had come other people that Dean had grown to like over the last couple of weeks. Garth, an incredibly nerdy guy, and Gordon, a street-smart kid.

Dean liked his new friends and had been a little surprised with how easily he fit in with them and how much they seemed to appreciate him. Another very good part was that they usually sat at a table in the cafeteria that made it easy for Dean to look at Cas, if she and her friends sat at their usual table. It seemed the only periods he had together with Cas was AP Math and lunch.

It was cool, though, Dean was a resourceful guy. He was sure he could find some way or another to get closer to Cas.

For one, the burn-outs hung out behind the bleachers (goddamn cliché if he ever saw one). They were kind of cool, in that detached way smoking weed and drinking could make a person. And they had no qualms about sharing with him (if he chipped in with some money, maybe perhaps?).

So he had thought about that, had shared a bum or two. But he liked Benny and the others more and besides, he had promised Sam to take his final year of high school seriously.

So becoming a permanent part of the burn-outs just to get an excuse to ogle Cas was a no-go.

His second brilliant idea was trying to join the football team. What a fucking riot.

Well, maybe he could have been good at it if he had put his mind to it but hell if he could concentrate when Cas was also out on the field. Plus, running around throwing a ball around like a jackass wasn’t that appealing.

Trying out for the cheerleading squad was out of the question. If he couldn’t even kick a goddamn football without straining a muscle, how the hell would he be able to throw girls into the air? Also, good luck concentrating on cheerleading with Cas bouncing around. Nope.

The day after Dean’s disaster of a football tryout Cas had asked him about it, sounding so cheerful that Dean wanted to splash himself with some cold water. Also wanted to die a little when he had to tell her that he didn’t make it.

But Cas didn’t sneer or scorn him. Just nodded as Dean explained why it had been a bad idea in the first place. Cas was always so understanding it hurt Dean’s heart.

Almost two months into the semester Dean wanted to call himself Cas’ friend but was fairly certain they were only acquaintances. He also wanted to shoot himself for being such a little pussy about this whole affair but that was another thing entirely.

Dean was usually pretty bold and suave with the ladies. His give-‘em-hell attitude was usually a sure fire with the females and he had always gone by the philosophy that you win some you lose some. But somehow it didn’t feel right playing it like that with Cas. Felt like she deserved more.

That plus the fact that Dean seemed incapable of holding a grown-up conversation with her. Why she was still talking to him he would never know.

The week before Halloween Dean found himself kind of dawdling in the corridor he knew Cas’ locker was in (stalker). Cas was standing by her locker, her friends around her talking about the Halloween party some girl was throwing this weekend.

Cas was smiling as she sorted through her books, two of her friends arguing over who got to wear what outfit. The sun was shining in through the windows by the stairs and it made Cas’ hair shine like a halo.

Or maybe Dean had accidentally taken some acid and was tripping balls. Gotta be one or the other, right?

"Cassie!"

Dean looked on as a guy in a peacoat approached the group of girls. Cas turned to him and so did the blonde (who Dean had learnt was called Jo, thank you very much). The others seemed uninterested.

"Fergus." Cas answered calmly. Jo looked angry for some reason but kept her trap shut.

"Told you not to call me that." The guy, Fergus, said with a grumble. Cas just smiled pleasantly.

"What can I help you with?"

"Going to Bela’s party?"

"Aren’t we all?"

 _Fergus_ rolled his eyes. "You know what I mean, honeybee."

He stepped between Cas and Jo so that Jo ended up behind his back, him crowding Cas against the still open locker door. Cas pressed her lips together and Fergus smirked.

"Fergus, please don’t."

Long-fingered hands casually flipped the hem of Cas’ skirt. A blue one today, not the cheerleading outfit, not every day. Cas shifted away and Fergus grinned.

Dean was stomping over before he was aware of it himself.

"Cas." He called in a booming voice, quieting everyone in the little group around Cas. "I forgot if we switched rooms today or not, walk me to class?"

Bold and stupid.

Fergus looked unimpressed. Cas’ eyes twinkled.

"Who the hell can’t walk to class on their own? Are you retarded?" Fergus sneered but thankfully straightened away from Cas. "Or maybe a scared little girl?"

Dean pulled himself up to his full length, towering over Fergus, chest out and eyes icy cold.

"Are you saying it’s wrong to be either one?"

"No one’s saying anything." Fergus grumbled but walked away without further arguments. Good, Dean would hate to have to punch someone in front of Cas. Or any of the other girls.

Jo snorted. "We could’ve handled him."

_Well handle it fucking faster then._

Dean ignored her and the retort he had at the tip of his tongue and instead turned to Cas.

"You okay? Who was that fucking douche?"

Cas rolled her eyes but smiled amusedly at Dean. "My ex-boyfriend."

Dean tried (and failed) not to look disgusted. "Really?"

"Don’t look like that." Cas laughed. "He had his appeals but they wore off, nothing odd about it."

"We all think he’s a douche." Lisa (the brunette) supplied and Anna (the red-head) nodded solemnly.

"Cassie’s too nice." Jo muttered and looked to where Fergus had disappeared.

Cas rolled her eyes but didn’t look angry or offended. Dean shuffled on his feet, uncertain if it was okay that he was still standing there but really not inclined to leaving Cas’ side. Fuck she was pretty today.

"Well." Anna suddenly said and Dean got a little nervous when he realized that he didn’t know if he had been staring at Cas or not. "Class is starting, we’d better get going if we’re gonna have time to go to the bathroom first."

With that she hooked her arms in Jo’s and Lisa’s and the three of them started walking away, Jo grinning at Cas over her shoulder. Dean watched them leave but turned back to Cas when she closed her locker.

"Aren’t Jo and Lisa in our class?"

"They are."

Cas started walking to the classroom and Dean followed.

"Don’t you want to go with them?"

Cas looked at him with an amused expression that Dean couldn’t explain the reason for. Girls usually went in throngs to the bathroom, right? Wasn’t that what Cas’ friends were doing?

"To the restroom?" Cas asked. She pulled a lock of her hair behind her ear. "I’m good."

Dean just nodded and tried not to be weird. They walked for a while in silence, Dean almost panicking when he realized they were soon gonna be at the classroom where they would split up. He wanted to talk to Cas some more, wanted to ask about Fergus, and shit, just wanted to _talk_.

_And maybe make out in a closet somewhere? Like this one, isn’t this a closet?_

They passed the door without mishaps.

"You look really good in that skirt."

Wow. Literal foot in the mouth.

Cas blushed a little.

"Thank you, Dean." She smiled.

"I mean, you look good in general." _Stop talking._ "Just, you know, blue suits you."

"My sister bought it out for me, said it brings out my eyes."

"Smart." God, it sounded like he was praising a fucking dog.

Just outside the classroom Cas stopped and turned to Dean. She looked shy all of a sudden and _oh my God_ was she aware that she was biting her lip? Was she trying to make Dean pop a boner right now? And it was working so well too, holy fucking shit. Impending boner alert.

"Are you going to the Halloween party?"

Dean tried to swallow. Too much movement now and he would really be sporting a sticky. Goddamnit.

"I’ve been thinking about it. Benny and the guys are going so…" he shrugged.

He wasn’t really a fan of Halloween or costumes so he had thought to maybe sit this one out but…

"Well, maybe I’ll see you there?"

But on the other hand, Halloween was awesome.

"Yeah, maybe."

  


*****

  


The Friday that week, the day before the party, Dean sat out on the bleachers openly looking at the cheerleading squad as they practiced. The visual stimuli was almost enough to get his overly excited dick to perk up but the constant tugging it had been subjected to in the last week kept it in check for now.

He was chewing on his lower lip, thinking his costume options through. Sammy had told him to make it easy for himself and go as a cowboy. Dean would probably go as a cowboy or not dress up at all. He had considered James Dean as well but supposed that would be considered "too little" in the way of an outfit.

He wondered what Cas would be going as.

The bleachers rattled as Benny climbed them. He sat down beside Dean and just looked on as the cheerleaders jumped, waved pompoms, and just generally cheered. Everything looked so goddamn smooth.

"So," Benny glanced at him. "Liking the cheerleaders, are we?"

Dean rolled his eyes.

"They’re fucking hot, you know that too."

"Sure do."

"So how does it work at this school?" Dean shifted to sit straighter. Cas was leading a cheer. "Gotta be on the football team if I wanna date one?"

Benny chuckled. "Nah. Clichés like that belong in the movies, brother."

Or at Dean’s last school but whatever.

"Well lucky me then because I sucked at football."

"You tried out?" Benny’s eyes gleamed with amusement. Probably shouldn’t have said that. Dean looked away but could still see how Benny’s eyes softened. "I think that Sarah Blake is dating one of the football dudes but otherwise it’s pretty mixed up." He said. "I don’t even think all of them have boyfriends."

Dean nodded casually, tried to play it cool but shit. His heart leapt up into his throat when Cas was thrown into the air. Her skirt flapped and she nailed the landing.

They sat for a while in companionable silence and Dean really appreciated that. Benny was by far his favorite friend and moments like this confirmed it.

"Got your eye on someone special?" Benny asked suddenly and Dean shifted, uneasy with sharing the exact details.

He had never really liked someone this much before so he felt open and exposed.

"Maybe."

"You see the one with the braid?" Benny pointed to one of the girls. She was pretty, Dean had noticed her before, but not nearly as pretty as Cas, don’t be ridiculous.

"Yeah?"

"You’d do well not to drool over her."

Dean turned to Benny and grinned. "Yeah? She taken?"

It was Benny’s turn to shrug casually. "She’s… Andrea and me we have this dance."

Dean laughed out loud and clapped his friend on the shoulder. "Don’t worry, man. I’m not gonna try and take your girl. I just like cheerleaders."

Benny smirked. "Don’t we all, brother?"

  


*****

  


Dean felt ridiculous. Sam had told him he wore the cowboy outfit really well and Dean had made the mistake of trusting his fourteen-year-old brother. Jesus, he looked like a goddamn fool.

Well, at least he wasn’t the worst. Garth had actually dressed like the dude from _The Fly_ , complete with a giant ass fly mask on his head. If Dean didn’t like Garth so much he would have been embarrassed to be seen with him.

On the other hand, Garth’s antics seemed a hit with the ladies and didn’t girls usually like men who could make them laugh? Dean didn’t know anymore, just felt like a wreck.

He straightened the hat for the tenth time since arriving (he needed to find somewhere to conveniently lose it or he would go mad), weaving his way through the throngs of people in this Bela girl’s house.

The music was loud and exceptionally bad. Dean had driven so he could go home when he wanted to, which he suspected would be the second after he’d seen Cas and gotten a heart attack. He’d spotted Jo and Anna and if Cas’ costume was half as slutty as theirs Dean wasn’t going to survive it.

He felt like he needed a drink to ease his nerves and to make him relax. With alcohol in his blood he was sure to be better at ignoring how atrocious the music was and how annoying anyone who wasn’t Cas was. But he had driven his beloved Impala and he didn’t want to crash her. Fucking shit, why had he even come?

And then he spotted Cas and it became blaringly obvious why he had come.

She was clad in a demure white dress, a pair of fluffy white wings on her back, obviously dressed up as an angel and for some reason the not-sluttyness of her outfit made her even sexier.

Dean had to hang back for a moment and just watch her as she talked to Lisa and some other people Dean didn’t know.

_Grip. Gotta get a grip._

Needed a grip on his dick but that would have to wait. Nice choice to wear restricting jeans. And he could blame his choice in pants on the costume so it didn’t look weird. Should maybe have thanked Sammy instead of bitching about the hat.

And then Lisa saw him and he just wanted to rip the hat off his head.

"Dean!" she called, loud and clear, enough to be heard over the music and fuckfuckfuck, Cas turned at her friend’s word.

And then Cas _smiled_.

Dean’s world felt off kilter and he really fucking needed to get a hold on his boner-situation. Needed to make it a non-situation.

But too late, Cas was already coming over, her friends in tow.

"A cowboy? How original." One of the girls said. Dean recognized her as Meg, one of the burn-outs. Funny she was hanging with Cas and her gang. Guess this school really didn’t get hung up on cliques. Good to know.

"Catwoman?" he responded with a cheeky grin. "How original."

Meg sneered at him but Cas’ smile was too dazzling for Meg to ruin this moment for him.

"I think it suits you." She said almost shyly. Dean’s cheeks were burning. Good thing the lighting was dim.

"You want something to drink?" Lisa asked.

Dean thought about his Impala but decided that he needed at least one drink if he was to calm down.

"Beer?"

"In the kitchen." Lisa answered with a smile and they all walked over to the keg.

Dean was impressed, whoever this Bela chick was she certainly didn’t cheap out, that was for fucking sure.

They drank for a while, Dean mostly sipping his beer (wanted to quaff it). Conversations were easy and Dean was relieved to find that he kind of fit in with these girls just as he had fitted in with Benny and the guys.

At some point Benny and Andrea appeared, looking disheveled in a decidedly pleasant way and conversations shifted over to them instead.

"Do you want to dance?" Cas bit her lip again and Dean’s knees trembled.

Dean _hated_ dancing but on the other hand this was a chance to have Cas pressed against him. Alone.

"Sure."

Cas led him to a bigger room (supposedly the living room with the furniture removed) and Dean couldn’t help staring at her perfectly round ass. Her fake wings bounced lightly when she walked and Jesus Christ, that dress was tight.

As they joined the rest of the dancers Dean noted thankfully that this was a regular chance-to-grind-against-each-other kind of dance. Nothing fancy, just a bunch of horny high schoolers smashing their privates together. Awesome.

Dean grinned down at Cas when she snaked her arms around his neck. She smiled coyly at him and yep, Dean’s heart was seriously in danger of beating out of his chest. Just gotta do this right and not get a boner. Difficult, considering that had been a problem ever since he first saw Cas but totally doable. Yep.

They danced for a while, pressed tight together but nothing overly indecent. Cas smelled wonderful, her eyes so big and blue that Dean felt like he was drowning in them. And that was good, staved off the immediate arousal for a while.

And then the song changed to something more… intimate but bouncy. It was hard to describe and it wasn’t like Dean cared to try either. Not with the way Cas smiled in recognition of the song and abruptly turned around to dance with her back pressed against Dean’s chest.

Her wings got smashed between them but they were small enough that it wasn’t a problem. Dean just put his hands on Cas’ hips and loved the way they felt. Sharp and agile. Goddamn, Cas knew how to fucking _move_.

She grinded her ass back against Dean’s crotch like she wanted him to cream his pants and maybe that wasn’t so farfetched a thought. He pressed in close, hands gripping her hips and his lips grazing her smooth neck.

She craned her head to the side and put her hands over his, swaying her hips to the music and _God_ …

_Don’t fucking moan her name right in the fucking ear._

It was a hard-fought battle.

It took very little for Dean to become fully hard and he was very sure Cas must be feeling his dick even through his jeans but she just kept grinding back, almost chasing him.

Dean’s hands flexed on Cas’ hips, holding her tighter. His dick wept in his underwear. Cas gasped when he thrust once against her, unable not to.

"Fucking hell, babe." He murmured, lips pressed to Cas’ heated ear. "So fucking sexy."

"Dean."

Fuck, the way Cas just kind of sighed out his name made Dean thrust against her again. He was _very_ glad that it was dark and the people around them were occupied with approximately the same thing he and Cas were engaged in. No one was paying them any attention and that was good because Dean didn’t think he could stop even if everyone was staring openly at them. In fact, that thought just made him even hotter.

"You make me so goddamn hard, fuck." He breathed harshly when Cas bucked back slightly. "Don’t wanna… I mean, you’re so fucking fine, wanna do things right."

Was he fucking drunk or what the fuck?! Why the hell was he admitting this to Cas for? How uncool.

Cas suddenly twirled around in his arms and he had an icy cold moment when he thought he had gone too far but then Cas was leaning in, just barely grazing their lips together.

"Wanna get out of here?"

Dean’s whole body shuddered. "Fuck yeah."

Cas took Dean by the hand and all but dragged him upstairs to an empty bedroom because apparently Dean’s life was a high school movie cliché. Not that he minded. Not when Cas closed the door before leaning against it and pulling Dean close.

Cas tasted sweet, probably like the drink she had been drinking earlier but beneath that was the underlying taste of Cas herself and sweet mother of everything sweet.

Dean groaned unashamedly and deepened the kiss almost immediately. Cas seemed to appreciate it. Her hands were fisted in Dean’s shirt and she tried to pull him closer.

His stupid hat bumped the door and he ripped it off only to throw it somewhere over his shoulder, not fucking caring. Goddamnit, two months of ridiculous pining and he _finally_ had his lips on Cas. It felt like a fucking dream.

"Dean." Cas moaned prettily and tried pulling him closer again.

But Dean was holding himself back, for a number of reasons. One was that it was fun to tease Cas, her desperate little gasps fueling Dean’s arousal so good.

Two was that he didn’t want to indulge himself and rub against her like some horny dog. Cas deserved better than that.

And three was that Dean was pretty sure he would come the moment he started grinding. Couldn’t really handle kissing Cas _and_ grinding. One thing at a time, at least right now.

"Fuck, baby." He mumbled, one hand on Cas’ hips, holding her still, and one hand coming up to caress her face. "You’re so fucking beautiful."

Cas blushed, Dean could see it even in the barely lit room. She looked down and bit her lip like she did when she was shy (much to Dean’s dick’s immense pleasure).

"Really?"

Dean just _had to_ kiss her hard. "What do you mean, really?" he grinned, cupping her head, finally feeling that hair between his fingers. "I’ve fucking wanted you since I first saw you. Prettiest girl in school."

God, Dean needed to come. But needed Cas to come even more. Needed her keening and writhing as Dean fingered her. Needed her to come again when he was inside her. Needed to ruin her for other men. Needed her to be his.

"Prettiest girl?" Cas repeated in a question.

Dean leaned on the door, his other hand still on Cas’ hip, massaging her. Kneading, almost.

"No doubt. Never seen anyone better." He licked his lips self-consciously. Cas was looking at him with an unreadable expression. "Not gonna lie, Cas. I’ve been with a couple of women before but no one’s affected me like you. I’m a fucking mess around you."

"So you’ve had sex with women before and now you want to have sex with me, a woman, too?"

What the hell kind of question was that?

"Yeah." Dean pulled back a little when Cas looked down. "But shit, you’re not just like another notch or anything, don’t think that." Oh, panic was slowly replacing Dean’s arousal. "I’m just shitty at expressing myself. I’m sorry, Cas."

"I think…" Cas looked away, pulled her arms around herself and looked small. Dean took an actual step back. "I need to go."

"Shit, Cas. I didn’t mean anything bad." Dean’s whole body felt cold. "I didn’t mean you’re not special, I…"

Fuck, he had just said the opposite, hadn’t he? He was seriously panicking now.

Cas looked up at him through her eyelashes, a very small smile playing on her lips. "I know, Dean. I know what you meant." Immense relief washed over Dean but it didn’t really last when he realized Cas was still leaving.

"Cas, what’s wrong?" he wanted to reach out but instead just stepped back when Cas turned to the door. "I didn’t mean to move so fast and I’m sorry I’m always running my mouth."

Cas stopped his desperate ranting by putting a hand on his arm. "Dean, you did nothing wrong." She smiled a sad little smile. "Can we talk on Monday? Can you give me the weekend?"

"Sure." Anything, he would give Cas anything.

Didn’t stop him from feeling miserable when Cas had left him alone in the dark room, though. Fuck, he had managed to screw this up, hadn’t he?

_Fucking shocker._

First time he actually liked someone and he had to ruin it by getting too eager. This was no one’s fault but his. And now Cas would think he was just some kind of pervert. Fuck, everyone would hate him.

He walked glumly downstairs and aimed to sneak away but of course Jo spotted him. Her look told him Cas had told her what had happened. He remained standing by the stairs as she walked up to him.

"Don’t beat yourself up."

"What?"

Hadn’t really expected her to say something like that.

She smiled kindly. "Just give Cassie some time to think and promise me that when you two talk you’ll keep an open mind. Cassie really likes you."

Despite everything he felt a little spark of hope at her words. "I promise." He mumbled, uncertain what she was talking about precisely but determined to obey her. Cas deserved it.

It was only when he got home that he realized he had forgotten the hat in that goddamn bedroom. Well fuck.

  


*****

  


"Are you going to mope all Sunday?"

Dean swatted away Sammy’s hand. "I’m not moping. I’m hungover."

"You weren’t even drunk yesterday and you got back before midnight. You’re _not_ hungover."

Dean wished Sam would stop being so goddamn perceptive all the fucking time and start acting like a kid again (although he was well into puberty and growing taller every day. Would probably grow taller than Dean, bastard).

"Leave me alone. I just wanna sit this day out." Get back to school, talk to Cas.

True to his word he had made no effort at contacting Cas. Not that he really could have even if he wanted to (he really wanted to) because he had no way to contact Cas. No phone number, no house address. No nothing.

Just the phantom feeling of Cas’ body against him and a thrumming arousal that went nowhere. He was even too morose to jerk off, although Lord knew he fucking needed it. Felt wasted.

"Fine." Sammy snorted and got up from Dean’s bed where Dean was curled into a ball of self-hate. "Just know you owe me for the cowboy hat."

Fucking Halloween.

  


*****

  


Dean was not proud to admit that he all but ran into school on Monday, leaving Sam by the Impala to fend for himself. Not that the squirt needed him but whatever.

Cas was standing by her locker together with her friends and shit, she looked as beautiful as usual. She had on a simple white button down, short sleeved and tight. Her skirt today was a salmon colored thing with black lace along the hem and oh boy, Dean needed to focus to not let his eyes wander.

He cautiously walked over to the group of girls but was of course easily spotted. Jo gave him a smile and Cas perked up at the sight of him.

"Hi, um…" he rubbed at his neck, feeling stupid.

But Cas took his hand before he could make a fool of himself. "Can you talk right now? Do you have time?"

If it had been up to Dean they would have been talking Saturday.

"Yeah."

Cas smiled a little and pulled him with her as she started walking away. Dean glanced over his shoulder and saw that Lisa was smiling at him too. Okay, so maybe he hadn’t screwed up too much? Maybe Cas was just gonna let him down real nice? Sure, that would feel awful but it would at least be better than him being a fucking pervert.

Cas didn’t say anything for the whole walk. Just led him by the hand (it felt fucking fantastic holding Cas’ hand) and Dean didn’t question where they were going.

He frowned in confusion when Cas started leading him up a flight of stairs he hadn’t gone up before but he still kept silent. Cas’ swaying ass was right in front of him too and fucking shit, that _skirt_. Dean loved lace.

The stairs ended in a door marked _Roof, no admittance_ and Cas just pushed the door open, clearly ignoring the sign.

"Wow." Dean mumbled and squinted in the sunlight. "Never knew you could go up here."

Cas quirked her lips. "People do it all the time. Mostly to hide from class, even though I suspect the teachers know."

She pulled him around the little house that made up the stair and door. On the other side was a park bench that looked suspiciously similar to the ones down in the quad. The floor around the bench was littered with old cigarette buds but the space was otherwise empty.

"Oh, good." Cas said and gestured for Dean to sit down on the bench. He did so slowly, only a little (a lot) sad to let go of her hand. "There was a chance that there would be people here. I wanted privacy."

Dean swallowed with a click that sounded overly loud to him. "Look, Cas—"

Cas held up a hand and Dean stopped immediately. "Dean, please let me talk first. I need to make this right." Make what right? Dean leaned back on the bench, just kind of staring at Cas who was standing before him, looking beautiful. "Are you okay with maybe missing homeroom?"

Dean wanted to snort because of course he was okay with that but he thought that would sound wrong.

"Of course." He mumbled. His hands curled into loose fists against his thighs when Cas smiled demurely at him. 

"I want to explain why I stopped us at the party." She started and pulled a stray lock behind her ear. "I really like you Dean but you said some things that made me realize I haven’t been completely honest with you."

Dean frowned in confusion. "Cas, I didn’t mean to make you upset."

Cas smiled. "You didn’t. I just…" she sighed deeply. "I just have some things to come clean about. And this is really my fault. I’ve been doing this for so long and everyone close to me knows." Dean felt as if his face was permanently stuck in that confused frown. Cas shifted on her feet. "I mean, my whole family knows, the teachers know, all my friends know. And it’s not a big deal anymore. I’m comfortable like this and I just…" she sighed again, more frustrated now. "I guess I kind of forgot how not everyone automatically knows, you know?"

"Um…" Dean had _never_ been so confused in his life. "Might wanna fill me in a little more, Cas."

Cas bit her lower lip and looked down, fisted her skirt slightly. "My full name is Castiel. I’m a boy and I just like to dress like a girl."

The world seemed to slow down as Dean was trying to catch up with what was going on.

"Uh…"

Cas sighed (again!) and lifted her skirt a little. Underneath she had on a pair of white panties and _holymotherofeverythingholythatwasadick_. And balls. A dick and balls trapped snugly in a tight pair of white panties.

Dean’s eyes budged out and his hands cramped against his thighs.

"I’m not like transgender, if you want a label." Cas continued but Dean barely heard her—him! Could only stare.

_It looks like satin. Wonder what it feels like?_

"I actually enjoy my gender, I’m just." Cas shrugged. "I’m a boy that likes to cross-dress. A transvestite I suppose, if you _have to_ label it. And gay, for the record."

Dean was slowly reaching out a trembling hand. Cas’ thighs were still as creamy white, her—his! (goddamn pronouns) eyes still as blue. Lips still as plump.

"I just really like you, Dean, and I hope this won’t come in between us. I mean, I get it that you thought I was a girl and that you might not like boys. I’m not asking anything like that, I just hope that we can at least remain friends. And I’m sorry things happened the way they did, I would really like for us to—what are you doing?"

Dean looked up at Cas’ question, only then realizing he had put one hand on Cas’ thigh and the other on his own dick. Also realized just now that he was fucking hard as a fucking rock.

"Uh, I, um…"

Cas’ grip on his (hah! Got it right!) skirt tightened but he didn’t lower it. There were so many things Dean wanted to ask right now but all his blood was in his dick. Plus, he had always been kind of a moron around Cas.

"Boobs?"

_Fucking hell, Winchester!_

Cas blinked. "Are asking about my breasts?"

"Maybe." Dean breathed. His hands were massaging now. Cas’ thigh and Dean’s dick alike. Cas’ eyes looked hooded but maybe it was just the sun.

"They’re fake. It’s just a padded bra. I don’t even wear one when I’m cheering, I thought you would’ve have seen." He bit his lip again. Dean’s dick jumped against his hand. "I’ve seen you watching us."

"You." Dean swallowed to get some goddamn moisture in his mouth so he wouldn’t sound like a frog. "I’ve been watching you."

"I was hoping." Cas tilted his head to the side, quirking his lips. "Do you like my panties, Dean?"

"Fucking hell, Cas." Dean groaned, rubbing his dick harder when he realized he was grazing the panties with his fingers. "So fucking hard for you."

_Careful now, don’t wanna scare him off again._

Dean didn’t know who that rational voice was but he tried his damndest to obey it. Even though his dick was already leaking and fuck, he had needed to come for too long. And here Cas was, standing with his skirt lifted for Dean to see everything.

Cas’ breath hitched at Dean’s words. "You want me?" he asked, his tone reverent. "Even though I’m a boy?"

"I just—fuck—I just want _you_." Dean gripped Cas’ hip, tried pulling him closer and Cas stumbled forward.

Dean was rubbing his own dick continuously now and it hurt to be trapped in his jeans but it hurt so _good_.

"Even if I dress like this? I tricked you, Dean."

"Didn’t do it on purpose, right?" Dean mumbled, hardly understanding his own words. Cas’ dick was certainly perking up at the sound of Dean’s hushed voice. It jumped against the restricting panties. Dean bit his own lip at the sight. "Fuck you look so hot, baby. I can’t even…" he looked up to see Cas staring down at him with eyes dark from lust. "I’ve never been with a guy, never wanted to. But I… Can I touch you? Please?"

Cas gasped sharply and then nodded, licking his lips once. He remained standing still as Dean let his hand roam over his body.

His thighs, his hips. Back to squeeze his butt and fuck, that made Cas’ hips jerk and he moaned lowly. Up and beneath the shirt to rub Cas’ stomach, toned and flat and so fucking smooth.

And down over Cas’ dick and balls. He felt smaller than Dean himself but still clearly manly. No fucking mistaking this part. Dean’s dick ached and jumped and spit out more precome.

"So fucking perfect." Dean rasped. Cas’ grip on the skirt had his knuckles go white. His hands were shaking. Dean rubbed furiously on his dick, so ready to come now. "Turn around, wanna see your ass."

Cas mewled (fucking _mewled_ ) and turned around. He lifted the skirt over the swell of his round cheeks and bent forward just a little, spreading his legs just a little, arched his back just a little.

" _Fuck!_ " Dean groaned and bucked up into his hand even as he was grabbing Cas’ ass, kneading the meat, pulling him closer. "Gonna make me fucking come in my pants, Cas. Fuck, baby."

Cas gasped. "Dean, are you…?"

"So fucking close." Dean’s breath came in short stutters. The bench was groaning along with his desperate movements. "Need you Cas, don’t care if you’re a boy or girl, need to be inside you."

Cas twirled around so fast Dean almost got dizzy from the sight of the flapping skirt. And then suddenly nothing mattered anymore because he had his lap full of Cas.

The boy’s knees pressed against Dean’s hips, his skirt spread out over their laps, his crotch against Dean’s, and his lips against Dean’s.

And Dean came with a strangled shout that Cas eagerly swallowed.

He gripped Cas hard, pressing the lithe body down against his dick even as he thrust up and fucking shit, he saw stars with how hard he came. Cas kept grinding down against him, his own hard-on prominent but he didn’t seem to be as desperate as Dean.

"You look so good, Dean." Cas mumbled, their lips still almost connected even if Dean was contributing very little to the kiss. His whole body went lax after his orgasm and he felt content to just sit there and let Cas pet him. "So handsome when you come for me."

"S-shit." Dean mumbled, barely aware of how hard he was clutching Cas. He nosed against Cas’ neck, reveling in how nice the boy smelled. _Boy!_ Fucking hell.

"Are you okay?" Cas mumbled after a while. Dean could feel that he was still a little hard even if it seemed to have diminished during their cuddling (oh boy, Dean was actually cuddling).

"Are you? Do you want me to…?" he didn’t know how to finish that sentence, which was ridiculous considering he had a dick too. He knew what could and should not be done to a dick.

_Fucking man up, Winchester._

But Cas shook his head and leaned out a bit so that he was merely sitting on Dean’s lap. "It’s okay. Sex wasn’t my intention anyway."

Dean blushed so hard it hurt. "I’m sorry."

"I’m not."

Cas’ cheeky grin made Dean feel marginally better.

"No but I mean it, Cas." The skirt’s material felt nice under Dean’s hands. "I get it that you wanted to talk and this was serious but I just… I guess I’ve been a little pent up over the weekend." He grinned and it was Cas’ turn to blush. He did so with a continued smile, though. "And while I’m fucking surprised you’re actually a guy it really doesn’t matter." He looked down and frowned a little. "Feels like maybe it should but with you... I dunno," he shrugged and smiled again. "I just don’t care."

"Oh, Dean." Cas mumbled and caressed Dean’s cheek. He was sure the gesture was meant to be comforting but Cas’ tone had been too sad.

"Guys have told you this before, haven’t they?"

"Yeah."

Dean pursed his lips. "Did they hurt you?"

Cas shook his head but stopped abruptly to seemingly think it through. "Not physically." He said with a sad smile and Dean wanted to murder anyone who put that look on Cas’ face.

"Who was it, Cas. Was it Fergus?"

Cas raised his eyebrows in surprise. His hands fisted against Dean’s chest. "Not only but Fergus was… Well, I liked him more than I had liked anyone else and he said he was okay with it but I don’t think he really was. He never wanted me to wear anything feminine to bed and," he shrugged. "I was okay with it for a while but I don’t want to hide this side of me. Not when everyone else seem okay with it."

"And you shouldn’t have to either." Fuck, Dean felt protective and weird and hot (and in love. Who the fuck said that?!). "Why the hell is he sniffing around you now for, then?"

Cas blinked and then smiled so knowingly Dean thought he should feel embarrassed but didn’t. "Guess he thinks we could still work things out."

"You can’t." It was Dean’s turn to blink at his own words. Cas was just looking curiously at him. "I mean…" he coughed self-consciously and glanced to the side. "I suppose you could and all but you can’t—I mean shouldn’t!" he sighed and forced himself to look Cas in the eyes. "What I’m trying to fucking say is that even if you work things out with him I don’t want you to get back together with him."

Cas tilted his head to the side. "Might want to elaborate that a little, Dean." Well fuck, Cas was clearly playing with him, Dean could see from the cheeky glint in the other boy’s eyes. And Dean loved it.

"Can we just forget the last ten minutes? I mean, not the conversations, those stay, but can we forget my embarrassing behavior and start over?"

"I don’t know." Cas said teasingly. "I might want to relive it when I jack off later."

Dean’s breath stuttered on an exhale. "Okay." He squeaked. "Well, apart from that…" he had to clear his throat before continuing. "Would you like to try and date me?"

Cas smiled his dazzling smile. Dean was glad he was already sitting down or his knees would have buckled.

"I would."

"Don’t be so hasty in your decision." Dean warned but shit, his chest felt ten times tighter with how elated he felt. "I eat a lot and have no table manners. And I swear all the fucking time. I have no money and I tend to put my foot in my mouth."

Cas put his hands around Dean’s neck and leaned down to kiss his lips chastely. "I think I can live with that. Also, I have a few suggestions of what you could put in that mouth of yours instead."

"Holy…"

The next kiss was much deeper, Dean’s hand tangled in Cas’ hair and Cas cradling Dean’s face in his. It somehow didn’t feel odd knowing he was kissing a guy, maybe it was because he had come to know Cas as a girl or maybe it was because Dean was so wrapped up in Cas in general that he didn’t care. He couldn’t say and he didn’t fucking care, not with how good it felt to have Cas writhing in his lap.

"We should get to class." Cas mumbled after what felt like an eternity of bliss.

"We should." Dean mumbled and shivered at the sound Cas let out when he pulled on the boy’s hair.

"I need to tell the girls about this."

Dean cringed a little. "Not _all_ of it, please."

Cas laughed and sat back a little. The come had dried in Dean’s underwear now and it was immensely uncomfortable but as long as it wasn’t visible he thought he could live with it.

"Maybe not, no." Cas conceded with a grin. "But about the part where you’d wanna date me even though I’m like this."

Dean frowned. "Don’t say it like that, there’s nothing wrong with you." He grinned suddenly and rubbed circles on Cas’ hips with his thumbs. "Still the prettiest girl in school. Prettiest boy too."

Cas laughed again, an elated sound that made Dean’s heart swell. "You know; the girls were really sure you’d be okay with this even though you were tricked. At least that you wouldn’t be angry."

"And you weren’t?"

Cas looked down and shrugged a little. "I hoped but since I’m a little more emotionally invested than them I guess it was easier for me to imagine the worst."

Dean got that and he wanted to say something comforting. But the truth was that he got stuck on _more emotionally invested_ and couldn’t help his own feelings fluttering about like stupid butterflies or something.

The actual truth was that he wasn’t certain about having sex with a guy and maybe dating someone like Cas would be difficult, Dean couldn’t tell. All he did know was how right it felt kissing Cas and how much he wanted more. More time with the guy, more sex. Just more.

"We’re gonna make this work, baby." He murmured intimately and Cas smiled coyly, making Dean’s heart swell again. God, he loved that feeling.

  
  



	2. In which Dean is in for a treat

**Summary for the Chapter:**

> Porny porness (those aren’t words! Lol)

**Notes for the Chapter:**

> Okay, so to those of you who were hoping for extended plot I say _sorry_. On the other hand, if you wanted smutty porn I say _you’re welcome_ :D

  
  


Dean and Cas had been going out for about a week now and Dean was slowly going insane with want. Fuck, Cas might be a man but he was still as beautiful and now Dean got to _touch_ him. Fucking heaven right there.

They had only managed a few sneaked moments together but Dean was nothing if not determined. He hadn’t watched all that gay porn for nothing, after all. And even though Cas seemed to enjoy the teasing Dean could see that the other boy was getting wound up too. Thank God.

Monday that marked their first week anniversary, not that Dean counted because who the fuck counted stuff like that (Dean, apparently), they found themselves alone in the library during third period.

They only had AP Math and lunch together but third period on Mondays were study hall for Cas and Dean’s History lesson had been cancelled for the day, thank fucking God. Dean didn’t think he could take not being with Cas much more. He was still hanging out mostly with his friends and sat with them during lunch even though he’d rather sit with Cas. They were taking it slow, which was good.

So freaking fucking fantastically good.

Cas was actually trying to accomplish some studying while Dean was mostly content with watching Cas and maybe snuggling in a little more than it was strictly appropriate. But hey, they _were_ basically alone and Dean _needed_.

"So Cas," Dean started in an intimate mumbled, by now well aware what his voice could do to the other boy. "You wanna do something this week? We could go to a movie."

His hands were on Cas now, Dean completely turned to him. One hand on Cas’ upper back and the other on his thigh. The skirt today was black and had black pearls along the hem. Dean played idly with them, eager to get underneath. Fuck he was such a fucking horndog. The muscle in Cas’ thigh twitched.

"I’d like that."

"Yeah?"

Cas turned to smile at him and Dean felt his whole body flush with arousal. Such a cheeky smile.

"Alone with you in a dark room? Count me in."

"Fuck, Cas." Dean breathed and leaned in, nosed along Cas’ neck when the boy turned back to his homework. "Trying my best not to pressure you here but fuck, I just wanna touch you."

Yeah, Dean was still really embarrassed about his behavior last Monday up on the roof. Jesus, he hadn’t even been able to hold it long enough to get out of his jeans. Had had to sit through the whole day with his underwear crusty with come. Disgusting.

So yeah, maybe Dean was trying to redeem that now, trying his best to not make every moment spent together sexualized but fuck, he was an adolescent man for Christ’s sake! And so was Cas, how the hell had he gotten so good at controlling himself?!

"I don’t mind you touching me, Dean." Cas responded, his voice low now too. Dean had to bite his lip to keep from groaning.

"This weekend, Cas." He murmured, leaned in close. Cas had given up on writing by now.

"What about it?"

"My dad’s away for work and Sammy’s going away with his soccer team. Some goddamn meet or something, I dunno."

Cas grinned and fuck, his cheeks were coloring slightly too. Dean pressed in closer, his hand on the boy’s thigh travelling up under the skirt a little.

"You saying you’re going to be alone?"

"Well, I was hoping you’d keep me company." Dean breathed against Cas’ ear. Goddamnit, Cas’ little gasp sent a spike of arousal through Dean’s entire body.

"The whole weekend?"

"Fuck yeah." Dean moaned. Lucky they were alone. Jesus, Winchester… "You could come over Friday after school, I’d cook some dinner for us, make it real nice for you baby."

Perhaps an overstatement since Dean barely knew how to make a good pasta sauce but he would do anything for Cas. Would fucking order in, just as long as Cas was happy.

"That sounds nice, Dean." Cas murmured. Dean kneaded his thigh.

"Want you to spend the night, Cas." He continued in the same breathless tone. Cas’ breath hitched. "We don’t have to do anything if you don’t want to, won’t force you to do anything babe but shit, _if_ you wanted to…"

"Yeah? What would you do then, Dean?"

Dean clenched his teeth against the groan that threatened to escape at the sound of Cas’ voice, thick with arousal.

"Would do you so good. Wanna fucking touch you, want to see you naked. Would suck you off, you’ll see Cas, I’d do anything to please you."

"Dean, please." Cas swallowed thickly. "Please stop talking."

Dean immediately leaned out a little. "Did I go too far? Shit, Cas, I just…"

Cas chuckled and turned to Dean, his pupils completely blown. Dean couldn’t breathe properly.

"I meant, please stop talking or you’re going to make me hard. Harder than I already am. Do you know how embarrassing it is to have an erection while wearing a skirt? It hides nothing."

Dean was hard like a fucking rock.

"You…"

Cas smiled and leaned in to peck Dean on the lips.

"You have no idea what your mouth does to me, do you?" he put a hand on Dean’s heated cheek, caressing it with his thumb. "I pleasure myself to the memory of moments like this. But we are still in public, Dean. And no matter how good the panties are at pressing down my dick they stop being effective after a certain point."

Dean’s breath was stuttering continuously now. "Cas, you’re so fucking sexy." He bit his lower lip, embarrassed at having admitted that. Cas just kissed him again. "I wanna do this right but I’ve never…" he huffed out a laugh. "I usually have better self-control."

And it was so difficult with Cas too. He wasn’t a girl but Dean had gotten to know him as one and it was difficult sometimes to know how to act. With a girl Dean would try and be more tactful but then again, some girls were extremely assertive in the bedroom and hated beating around the bush. And just because Cas had turned out to be a guy didn’t mean he was just as horny as Dean, everyone was different.

But Cas accepted Dean however he acted, it seemed.

He got a new kiss for his honesty and Cas was still smiling.

"I like everything we do, Dean." Cas stated with conviction. "And I would love to spend the weekend with you."

"Cool." Dean mumbled, still blushing but smiling too now.

"What movie did you have in mind?"

For the weekend? No, right, he had asked Cas to go to the movies sometime during the week. Fuck, Dean was all over the place.

"You know what, you decide. I just…" he cleared his throat a little. "I’m just gonna go to the bathroom real quick."

Cas blinked and then a sly smile spread over his beautiful face. "I’ll wait here."

Dean hummed in agreement and then all but fled to the restrooms. Fuck, just thinking about Cas all hard and squirming in his seat like that made Dean hard enough not to think straight.

It was the image of Cas’ dick tenting his pretty skirt that made Dean blow his load. Hard and forcefully enough to splash the wall fucking _behind_ the toilet. Christ.

  


*****

  


Cas had wanted to watch Batman vs. Superman and how fucking awesome was that? Dean even shared his popcorn, that was how awesome Cas was. Sam’s eyes would have budged out at the sight of Dean actually _offering_ Cas his popcorn. Yeah, Dean was pretty gone over this boy alright.

"Dean." Cas bit out through clenched teeth.

They were sitting way at the back, alone on that row and the closest people four rows in front of them.

"Hm?"

"Please don’t."

Dean withdrew his hand from Cas’ thigh.

"I’m sorry." He tried sounding it too, tried not to grin evilly.

Cas glared at him but the look was kind of lost in the darkness. "You know I can’t control myself."

"Actually I’m starting to believe you’re the master of control." He really grinned this time and put his hand back. "I just wanna hold your hand."

Cas grabbed his hand forcefully. "Then learn anatomy."

They sat for a while, holding hands and oh boy, that was unexpectedly nice. Dean couldn’t help rubbing his thumb against Cas’ smooth skin though. And he was soon pressing and rubbing almost rhythmically.

He didn’t actually think about it until Cas let out a small gasp. When he looked over he could see the boy’s eyes scrunched shut and his whole lower body squirming. Fucking shit.

"You okay there, babe?" he mumbled, his voice covered by the loud movie (even Superman flying was loud).

"Peachy." Cas squeaked out. Dean wished it wasn’t so dark, wished he could see just how peachy Cas was.

He leaned over, putting his mouth to Cas’ ear and his other hand on the boy’s thigh, rubbing lightly. Cas’ hips lifted off the seat a little.

"So fucking hot. You know that, right?"

"Dean, I’m gonna get—shit—gonna get hard."

Hearing Cas swear always got Dean hard.

"No one’s gonna know."

"But…"

Dean licked the skin under Cas’ ear and Cas gasped sharply. They were really fucking lucky it was a loud movie (enough to rattle the walls with the sound) and that everyone else was too far away.

"You make me hard all the fucking time, baby. Do you even know how often I have to sneak off to the bathroom to jerk off? Want you so bad."

Cas was rocking his hips slowly now, his hand clenching Dean’s so hard it would’ve have hurt if Dean could register anything other than pleasure right now. Cas was usually so in control, to see him like this was so fucking delicious. Too delicious to pass up on.

Dean had to bite his cheek to keep from groaning when he put his hand on Cas’ hard dick. Cas flung his head back, pressing it against the headrest, his eyes open wide. His breath punched out of him and Dean loved how it sounded.

"Sorry." He mumbled but didn’t remove his hand. "I should stop."

If stares could kill…

"Don’t you dare stop _now_."

Dean rubbed the heel of his hand against Cas’ dick. It jumped and Cas chased his hand with his hips. He let go of Dean’s hand to clutch the armrests instead and Dean lifted the skirt to slip his hand beneath, feeling Cas through his panties.

They had done this once before. Cas panting in Dean’s lap and Dean thrusting up against him even as he fondled Cas’ dick. It had ended with the both of them coming in their underwear (again!) and Dean was starting to think he was doomed to never hold out long enough to actually see Cas naked.

_This weekend._

He would take such good care of Cas, fucking hell would he ever.

Cas tried to remain as still as possible, Dean could tell, but it was a losing battle.

"Don’t… don’t take me out."

Out of the panties, Dean suspected, because then the come would get everywhere.

"It’s okay, baby." Dean mumbled and reached back with his unoccupied hand. "We got napkins with the popcorn."

"H-hurry."

Fuck, Cas was biting his lower lip, his hips thrusting up in sharp little motions. Dean was steadily massaging his dick and fuck yeah, he could feel it expand in the wake of his release.

"My baby gonna come?" he cooed breathlessly. He fumbled with the napkins, almost dropped them. Cas’ face was scrunching up in pleasure. "Fuck, wish I could get on my knees and suck you. Just put my head under your skirt, let you fuck my face."

Cas’ eyes flew open as he came forcefully against Dean’s palm, come shooting through the flimsy material of the panties. Dean sucked in a sharp breath through his nose and tried to cover the other boy’s dick with his hand as much as possible to save the skirt. Shit, he hadn’t even had time to get the napkin under there.

When Dean lifted the hem of the skirt to try and get the napkin on Cas’ dick to wipe it off the boy turned and kissed Dean forcefully. He twisted in his seat, pressing in as close as he could with the armrest still between them, his hands in Dean’s short hair.

"So good, Dean." He mumbled in a slurry voice. Fucking perfection.

Dean grinned. "Prettiest ever, Cas."

  


*****

  


Longest fucking week of Dean’s life. Seriously. But finally it was Friday so he had just to get through this day and then Cas would be his for the weekend.

Cas had said he needed to go home to pack first and that was fine, Dean thought. That gave him time to drive Sam to his soccer team. A part of him had wanted Cas and Sam to meet and Lord knew Sammy was really eager to meet Dean’s boyfriend (God, that word! Dean loved it) but he supposed they would have time to do that some other time. Dean couldn’t wait for that either. Sammy was going to love Cas, Dean was sure. Cas was so smart, and funny, and pretty, and—

Dean needed to get a grip.

He grinned over at Cas who was sitting with his friends over at their regular table. Jo and Anna noticed him and made fake heart-eyes at him just to tease him. Cas rolled his eyes fondly at their antics.

"So, any plans for the weekend, brother?"

Dean had to literally tear his eyes away from Cas.

"Maybe."

Didn’t have to tell his friends _everything_. Still, they were guys too and they could all probably read his expression like an open book.

"As long as you stay safe." Garth said sagely and Dean chuckled at him along with Benny.

"Sure thing, Grandpa."

Garth scoffed and continued eating his burger.

"So you’re really going out with that Novak kid, then?"

Dean turned to Gordon, confused by his tone and even more so when he saw his friend’s sour expression.

"Well, yeah." Dean shrugged casually. "Only two weeks but I’d say we’re dating now."

"Didn’t know you were gay, ‘s all."

Dean frowned and so did Benny.

"If you need a fucking label I’d say bisexual but what does it matter?"

Gordon scoffed but unlike when Garth had done it this sounded much more derisive. Ugly.

"And you’re okay with him dressing like that?"

"Why wouldn’t he be?" Garth asked, sounding thoroughly confused. "Cas’s dressed like that since we got to high school, hasn’t he? And he’s been into guys since before that. It’s not like it’s news."

"It’s just weird."

Dean had to put down his fork lest he might bend it in half. "Excuse me?"

Gordon rolled his eyes. "A guy dressing like a girl is weird in itself, isn’t it? But for you to encourage it? I mean, do you pretend he’s a girl when you fuck him?"

"Don’t talk like that." Benny murmured in his southern drawl and it was good he interfered. Dean would hate to make a scene.

"No but really. Are you even sure you’re bisexual, with him looking like that it’d be easy to pretend, wouldn’t it?"

Okay, screw not making a scene.

"Do you fucking hear yourself?" Dean snarled, his voice loud enough to draw the attention of the table next to theirs.

Gordon shrugged carelessly. "I’m just saying, if you’re okay with him being a guy then why does he have to dress like that?"

"Are you saying Cas dress like that to lure guys in?" Garth asked, astonishment in his voice. Dean was shaking with anger.

"Well it fucking worked, didn’t it?" Gordon exclaimed and gestured to Dean. A girl from the next table gasped in indignation. Benny put a hand on Dean’s knee, keeping him grounded.

"I think you should leave now, brother."

"What?"

Garth nodded. "I think that might be a good idea. We’ll talk to you later, Gordon."

Gordon looked between the three of them and then stood up abruptly, almost growling in anger as he stomped away, leaving his lunch tray behind.

"It’s okay, Dean." Garth said when they were alone. "Don’t think about him."

"Thank you." Dean mumbled and tried to get his feelings under control. Needed not to make a larger scene or Cas would notice and he could never hear about this. Dean needed to protect him from shit like this. "Sorry for coming in between you guys."

Benny shook his head solemnly and clapped Dean on the shoulder. "Gordon’s always had a hard time accepting changes. He’ll come around."

Dean wasn’t so sure he ever wanted Gordon around anymore at all.

"Guess Cas dressing like that meant nothing to him when Cas was just another student in school." Garth mused as they slowly began eating again. "It probably got a bit too real for him."

"If you guys have a problem with this you’d do well to say so now."

Benny and Garth met Dean’s defiant stare with calm looks.

"Not going anywhere, brother."

"You know," Garth said suddenly, looking peevish. "Might be that Gordon fancies Cas himself. Or you."

"That’s ridiculous." Dean scoffed. "This isn’t a high school movie." Despite numerous events stating otherwise…

"Cas _is_ awfully pretty, even for a guy." Benny drawled with a smirk.

Dean’s skin crawled at the thought of Gordon touching Cas like that.

"Well he can’t fucking have him. He’s mine. And no one that talks about Cas like that deserves him anyway."

Benny and Garth grinned eerily similar grins. Dean jerked when he felt a hand on his shoulder and when he turned he saw that it was the girl from the other table. She had flaring red hair and a _Who’s your daddy?_ t-shirt sporting Darth Vader’s helmet under the text.

"Good for you." She said, flashing him a happy smile.

Dean smiled a little up at her. "It fucking is."

  


*****

  


Cas showed up an hour after Dean had dropped Sammy off. The little squirt (not so little anymore, Dean) had been thoroughly disappointed that he wouldn’t get to meet Cas but Dean had promised him that next time he would bring Cas home when Sam was home too. And maybe dad? What would dad say about this, Dean wondered? Dad was pretty chill but he was also an ex-marine. Still, just because he was marine didn’t mean he had to be a homophobe, right? That was just prejudice, thinking like that.

Dean decided to worry about dad next Tuesday when the man was due back from his work.

Cas was wearing a frilly white and pink skirt and a matching top. He had his hair pulled back by a headband and just looked so goddamn good in general that Dean’s mouth watered at the sight of him.

It was not the same clothes that he had worn in school and Dean felt hot with affection at the thought of Cas actually changing to try and look nicer for Dean. He even had mascara on, Dean could tell in the bright sunlight.

"You look amazing, babe."

Cas smiled demurely and looked down while tucking his hair behind his ear. And fuck, was he squirming a little on the spot? Had he been nervous?

Dean felt as smooth as a goddamn log when he offered to take Cas’ bag for him.

Cas got the cursory walkthrough of the house but Dean didn’t let them linger for too long (especially not in his bedroom). Mostly because he had pasta cooking on the stove but also because he couldn’t seem to keep his hands to himself. Didn’t really need to put a hand on Cas’ lower back when they walked up the stairs, for example.

"This is a nice house." Cas said as he sat down on the barstool on the opposite side of the kitchen counter.

Dean smiled. "You don’t have to sugarcoat it, Cas. It’s kinda rundown but at least it’s home."

Cas smiled too. "You’ve made it nice, then."

Fuck, Cas always knew exactly what to say.

Dean focused on the food for a while, Cas talking a little about his own house and his family. Big, liberal parents, religious in a laid-back way. They seemed nice when Cas talked about them.

"It smells good." Cas said when Dean was plating.

"It’s only pasta with hot sauce but you know," Dean shrugged and scraped what was left on the bottom onto his plate. Didn’t want Cas to have it if it had gotten a little burnt. "It’s food."

Would have wanted to take Cas to one of those fancy restaurants that had menus Dean couldn’t pronounce but whatever.

Cas put a hand on Dean’s arm when he sat down beside him. "It’s perfect, Dean."

Dean didn’t think he had blushed quite so much before he met Cas.

They ate in comfortable silence for a while, Cas making these little appreciative noises that he needed to watch out with or Dean would fucking jump him right here in the kitchen.

_Calm down. You need to fucking calm down. You’ve got all weekend. Do it right for fuck’s sake._

It was difficult, though.

"Are you going to tell me what Gordon was upset about?"

Dean’s face scrunched up in confusion. "Uh…"

"He stormed out of the cafeteria."

Oh. Dean sighed and barely refrained from squirming. He didn’t want to talk about this. Wanted the weekend to be just about them and nothing foul. Wanted Cas happy.

But Dean couldn’t and wouldn’t deny Cas.

"He said some shit about you and Benny asked him to leave."

There, enough about that.

"What did he say?"

Fucking hell!

But, okay, Cas didn’t look upset. Just looked curious and Dean could do this without getting angry all over again or being a total douche for no reason. Could be fucking grown up.

He shrugged (because that’s mature…). "Just, you know, stuff about you dressing like a girl. Questioned my sexuality. If… Well, I suppose he meant that I couldn’t be so sure I like boys if you keep dressing like that. Like you would confuse me or some shit."

"Do you feel like that?"

"Hell no!" Dean turned to Cas who looked awfully smug. Dean frowned in confusion. "But you already knew that, didn’t you?"

Cas smiled to himself and went back to eating. "Charlie told me the gist of it."

"Charlie…?" _The red-head._ "Fuck, now I’m embarrassed." He groaned and hid his face in his hands.

Cas laughed out loud. Dean _loved_ that sound. "Don’t be." Cas successfully tried to pull Dean’s hand away and leaned in to kiss him lightly. "You defended my honor, from the way I heard it."

"God, can we talk about something else?"

Cas laughed again. Like a soothing touch to Dean’s tired soul. "Whatever you want, Dean."

_Want to rip that skirt off you and fuck you. Wanna get to your no doubt perky nipples. Wanna bite ‘em._

Getting. A. Grip.

Dean huffed out a shaky laugh himself. "Sorry, I’m not that good at long-term relationships."

Cas looked smug again. "You see us being long-term?"

"Baby, from my standpoint we’ve been going out for two weeks, that _is_ long for me."

Instead of being appalled that Dean apparently had never managed a real relationship Cas looked awfully satisfied with the revelation.

"What’s the craziest you’ve ever done? Sex-wise."

Jesus, way to get Dean’s mind back on that track.

He hummed and chewed the last of his food for a while, thinking his escapades through.

"One summer I was working as a pool boy in the neighborhood we were living in then. Fucked a housewife in the toolshed while her husband was outside mowing the lawn. He walked by the window twice but didn’t see anything."

Cas actually threw his head back laughing and Dean could do nothing but stare at his smooth neck and smile too. Had he been scared that Cas would think he was disgusting? Yes. Felt good to get a reaction like this, though.

"That’s so _lewd_." Cas exclaimed with mirth.

"It’s not the worst thing. Turned out she wanted more of my ‘service’, offered to pay me."

"No!"

Dean nodded solemnly at Cas’ scandalized face. "True story."

"What did you do?"

"Accepted the money. Hell, Sammy needed new clothes and dad was…" Dean shrugged. "Mom died when we were little and dad only recently got a grip." He grinned to chase the depressing atmosphere away. "Went around the neighborhood to see if I could find more lonely housewives. Had a little system worked out by the time dad decided to move us."

Cas was looking at him with sad eyes and fuck, he had managed to fuck up after all, hadn’t he? Daring sexual escapades were one thing but outright whoring himself out was another, wasn’t it? Goddamnit, Dean was too ugly for Cas.

Cas broke into his reverie by leaning in and hugging him, kissing his cheek.

"How old were you?"

"Sixteen."

"You’re so brave, Dean."

Fucking shit, this was not what Dean had planned for the evening. He needed to get a hang on his emotions around Cas. It was too easy to slip up. There was just something about Cas that made Dean feel vulnerable in a good way, made him want to share all of himself. And desperately wanted to be accepted.

"Shouldn’t have told you that, though." He muttered because apparently he _had to_ run his mouth all the time. Where was his fucking filter?

"You don’t have to hide with me, Dean. I want all of you."

Was Cas a goddamn mind reader?! A shudder went through Dean and he didn’t even know why. Cas hugged him closer and the next kiss landed on Dean’s mouth.

Soft and tasting of the sauce. Dean allowed himself to moan at the much-desired contact. They both tilted their heads and deepened the kiss. Wet and hot tongues sliding together in the most intimate of dances and Dean was shivering for real now.

"You’re the brave one." He mumbled against Cas’ lips. His hands wandered but he tried to stay over the waist.

Cas just smiled and kissed him again.

  


*****

  


So apparently Cas hadn’t seen the latest Star Wars and Dean felt a pressing need to change that. Cas had just laughed at him but had snuggled up on the couch as Dean chatted about the movie, trying not to spoil it but barely able to contain himself.

It took very little time before Cas slid over the couch to curl against Dean and Dean immediately put his arm around the other boy. Cas smelled so fucking nice, like a meadow or something more poetic. Dean wondered if Cas had worn perfume too.

Cas’ skirt had risen a little when he had pulled his legs up to rest them on the couch, folding them beneath himself. Dean shifted and let his hand fall down to rest on Cas’ hip.

Han Solo and Chewie found Rey and Finn and Cas’ hand clenched in Dean’s t-shirt when Dean started kneading his hip.

Felt so fucking good to just be sitting here like this with Cas. Felt like home.

Dean kind of wished he had had time to rub one out, though. And that little make-out session in the kitchen hadn’t really improved his dick-situation either. Plus, there was all that emotional shit that had just thrown him off kilter.

Dean really kind of needed Cas right now. And Dean sucked at talking, needed actions to make it better.

Cas shifted closer when Dean gripped him harder and when Dean looked down he was met with the other boy staring up at him with hooded eyes.

"I don’t want to seem too eager, Dean, but…"

That goddamn lip-biting was going to be the death of Dean, for sure.

"Sorry, Cas." He mumbled. "Trying to do right by you but I’m really fucking horny, all the fucking time."

Cas surprised him by grinning widely. "You seem to forget I’m a guy too, Dean. Do you think I’m not horny?"

Dean knew he was or that stunt at the movies earlier in the week would never have worked but shit, hearing Cas say it was _awesome_.

"Just don’t want you to think I’m rushing things."

"It’s been two weeks, Dean. Tell me what you want."

 _Cas_ was awesome.

The movie was still playing in the background but who the fuck cared about Rey being kidnapped when Cas’ lips were on his? God, they just fitted so perfectly together.

"Wanna see your dick tenting your pretty skirt." Dean murmured and rubbed Cas’ chin with his thumb. Cas’ breath hitched. "Wanna feel your dick against mine, wanna come on you."

"Dean."

"Fuck yeah, wanna hear you moan my name, baby."

Cas writhed against him, pressing closer. He unfolded his legs to sit straighter and Dean wasted no time slipping a hand under Cas’ skirt.

And fucking shit, Cas was already leaking in his panties.

"These feel like lace, you wore your fancy panties for me, baby?"

Cas clung to him and bucked up to chase Dean’s hand. "Want to be pretty for you."

 _Fucking fuck._ Eloquent…

"You so are, Cas, baby, prettiest I’ve ever seen."

Dean was torn now between wanting to see Cas in the lace panties (because lace was _the best_ ) and putting his own dick in there to feel it.

He slowly pulled Cas out of his panties.

"Tell me no and I’ll stop, Cas." He breathed reverently against Cas’ neck, tasting the boy on the air between them.

"Want you, Dean."

Dean nodded jerkily, unable to answer properly when his eyes landed on the way Cas’ dick was holding up his skirt. No one would mistake what was going on if they saw this.

Dean’s breath stuttered and his own dick jumped when he wrapped his hand around Cas on the outside of the skirt, trapping Cas’ erection in an embrace of frilly cotton.

Cas moaned out loud, unabashed and beautiful, his head resting back against the couch as Dean started jerking him.

"Looks so fucking perfect, babe." Dean groaned.

His hips jerked when Cas put a hand on his hard-on.

"You too, please Dean."

"Yeah, fuck yeah."

Their breathing was clipped, panting. Hot air mixing and making everything sweltering and then Dean was free from his jeans. Relief washed over him, pressing a dollop of precome out of him. Cas pressed his thumb against the slit, spreading it out and down over the frenulum, making Dean see fucking stars.

"Want you inside me, Dean."

Dean’s hand on Cas sped up.

"Me too, gonna do you so good, you’ll see." Promises, promises. Dean needed to get control over himself so they would actually get to that part sometime this fucking year. But shit they still had time and Dean couldn’t breathe with how much he wanted to come right now.

"Come on, Dean." Cas suddenly urged and pulled on Dean so that they fell back on the couch. Cas on his back and Dean between his open legs.

The skirt rustled as they wrestled it out of the way as much as they could. Dean made an embarrassingly garbled sound when their naked dicks pressed together for the first time and why the fuck hadn’t anyone told him how fucking amazing this would feel?

Cas’ dick was hot and hard and pulsing against Dean’s and when Dean got his hand around the both of them Cas mewled and started thrusting almost immediately.

They were both uncut and leaking precome enough to slick the way but it was burning a little, that was true. Not that Dean fucking cared when Cas greedily pawed at him to get him to lean down and kiss him.

The kiss was sloppy and half-assed at best but Dean just really couldn’t concentrate properly.

"Gonna come so soon, baby." He moaned. Cas rolled his hips up into the tight grip. "You feel so fucking good, you have no fucking idea."

Cas’ laugh was breathless and perfect. "I think I kinda do."

Dean groaned and hid his face against Cas’ neck, licking and nipping the delicate skin there.

"Gonna fucking ruin your pretty skirt, tell me I can. Fuck, Cas, wanna come all over you."

"Oh." Cas’ whole body locked up. "Oh, Dean." He bucked up one last time before spilling all over Dean’s hand and dick, come shooting up into the folds of his own skirt and Dean couldn’t take it.

Cas was spasming beneath him, his dick pumping and pulsing and Dean came with a shout. He buried closer and breathed harshly as he stripped their dicks, working every last drop out of them.

He collapsed on top of Cas when he was done and Cas wrapped his arms around Dean and kissed his hair.

  


*****

  


When Cas came back from the bathroom after having made himself ready for bed he wore a simple t-shirt and a pair of blue boxer-briefs. Guy clothes. His hair was down and his mascara was gone too.

Dean sat up in his bed (big enough for two, thank you dad!) and Cas shuffled by the door, looking down at the floor.

"Cas." Dean said softly and reached out a hand. "Come here."

Cas looked up and his face was torn between relief and cautiousness. He stepped forward slowly and sat down on the bed when Dean pulled on his hand. He looked nervous and stiff. Dean leaned in and kissed him slowly, tenderly.

"Did you think I wouldn’t like you when you weren’t all dressed up?"

Cas swallowed. "I didn’t know what to think."

"Your past boyfriends have been fucking dicks, Cas."

Cas huffed out a shaky laugh. "I’m starting to think so too."

Dean grinned and scooted over to make room for Cas to crawl into the bed too. "Not that I wouldn’t love some lingerie, baby. Or we could sleep naked, I just wanna sleep together with you."

Cas smiled, much brighter now, and curled himself into a ball for Dean to spoon.

"I want that too."

"You’re always the prettiest. And mine."

If Cas could purr Dean was pretty sure he would.

  


*****

  


Dean woke up first, some moron honking at (probably) some other moron just outside his bedroom window. He groaned in dissatisfaction and rolled over, his grumpy expression immediately replaced with a smug grin when his eyes landed on Cas.

The other boy was on his back, the comforter kicked down to his feet, still sleeping serenely. His dick, on the other hand, was very much awake by the look of it. It tented his underwear just beautifully.

Dean supposed it _could_ be hard because Cas actually needed to pee. Dean’s dick got like that sometimes, which he suspected happened to all guys. Or it could be morning wood.

Dean’s grin became decidedly wolfish. Mmm, morning wood…

He slid closer as carefully as he could, not wanting to wake Cas just yet.

How anyone could not think Cas was beautiful without his outfits and make-up was fucking beyond Dean. He still had his high cheek bones, plush lips, so soft and pink. His hair was still lush, his eyes still as shining. And his body… just damn.

Okay, so he didn’t have boobs and he wasn’t curvy like a woman but Dean just loved the shape of Cas anyway. Sharp hipbones, a lithe build. Just so fucking _agile_. Yeah, Dean could live without boobs. Especially since he had recently discovered the joy of another guy’s dick and oh boy, Cas had an _awesome_ dick.

Nicely shaped and very responsive.

Actually, now that Dean thought about it, he hadn’t really gotten a good look at it naked, not really. Last night had been close but there had been a lot of skirt everywhere and Dean hadn’t exactly been paying attention.

Cas’ hips twitched when Dean pulled down his boxer-briefs enough to spring his dick free. Cas sighed in his sleep and pressed the side of his face against the pillow.

Fuck, Cas had such a nice _shape_. It was… well fuck, if a dick could be pretty (Dean needed a better adjective or he would wear this one out) then Cas’ dick certainly was. Not a real shocker there, though, considering it was attached to Cas.

It bobbed a little on its own and Dean soon took pity on it and grasped it lightly. Cas gasped just wonderfully. Dean was hard himself but it was fine for now, could grind it a little against the mattress and be satisfied. He just kind of needed to explore Cas for now.

Because okay, Gordon was a douche but he had had kind of a point. Really, Dean had been very sure about his choices and of the fact that Cas was a boy (since Cas had told him at least…) but this, right now, this was the first time he had really touched Cas as a boy. Or, well, Cas didn’t identify as a girl so that wasn’t true but still. Like this Cas was clearly manly and Dean was thrilled to realize he still wanted the boy so fucking much.

Cas’ breath shuddered when he thrust up into Dean’s loose fist. It felt good having Cas fuck his hand like that. When he tightened his grip Cas fucked harder. Delicious.

"Dean." Cas moaned but when Dean looked up it seemed the boy was still asleep.

"Fucking hell, baby." Dean groaned. Goddamnit he was hard now. Cas was leaking precome over his fingers. "That’s right, Cas, moan for me."

Cas’ eyes fluttered open at Dean’s words and the world kind of froze for a moment there.

"Dean?" Cas asked and unclenched his hands from the sheet beneath him.

"Uh, hi." Dean grinned shyly. "You just… um, looked like you needed a hand."

Cas blinked owlishly, obviously trying to dispel the last of his sleep. And then his eyes landed on Dean’s hand, still wrapped around his pulsing dick.

"D-Dean." His whole body jerked and then his hips were thrusting again, harder, faster. He whimpered when Dean aided by stripping him sharply, adding a twist to the end. "Gonna come."

"God yes." Dean moaned and pressed closer, rucked up Cas’ t-shirt to get to his nipples. Fucking perfection right fucking there. Tight and pink, pebbled and practically waiting for Dean’s mouth.

Cas wailed in pleasure when Dean wrapped his lips around one of his nipples. It only took a few more strokes before Cas was coming hard, his face scrunched up in an expression that could easily be mistaken for pain if it hadn’t been for his hot dick spurting come all over his stomach.

"Oh, Dean, you…" Cas gasped desperately, trying to catch his breath but only barely succeeding.

"You’re so fucking hot, Cas, can’t keep my hands away."

Cas moaned again and pulled on Dean’s hair until he crawled up to kiss him deeply.

"You too, wanna do you too."

"You know," Dean grinned. "We could take a shower."

The thought of seeing Cas completely naked _and_ slick with water made Dean’s dick jump painfully where it was pressed against the bed.

Cas grinned the lewdest grin Dean had ever seen and not five minutes later he found himself in the shower, towering over Cas as the boy sucked him off, water cascading down over them.

Dean came within a record-breaking thirty seconds and spent the rest of the shower trying to make up for it by washing every inch of Cas’ body, even though Cas insisted that he had loved it.

Still, you warn someone before coming hard down their throat, it’s just good fellatio etiquette.

  


*****

  


They spent the Saturday just breathing each other in. Hung out as friends but with the added benefit of that special spark between them. Dean loved it.

They ate breakfast out by the TV, actually finishing the Star Wars movie this time and afterwards Dean taught Cas how to play Call of Duty, which he proved extremely adept at.

Cas was back to wearing girly clothes and Dean couldn’t honestly say which he liked best. Only knew that the blue skirt Cas once again wore definitely was Dean’s favorite. Cas’ sister had been right; it really did bring out his eyes.

When it got time for dinner Cas offered to cook them something, which led to them driving to the grocery store for some shopping.

_Like an old married couple. No, don’t get ahead of yourself. Shut up, let me have this._

It was pouring down when they eventually finished in the grocery store, the rain so thick they could hardly see the cars in the parking lot. It had been extremely warm for November but with the rain came the chill and they looked morosely out through the curtain of rain. Dean wished he had a Batmobile.

He shrugged off his leather jacket and put it around Cas’ shoulders.

"Dean, no, you’ll get cold."

"It’s okay." Dean grinned. "Stay here with the bags and I’ll go get the car."

Cas frowned. "Then you really _should_ wear your jacket."

"Just you watch." Dean winked. "I’m quicker than the Flash."

Dean was of course drenched by the time he got in his car but whatever, a little rain never hurt nobody.

"Except maybe Noah." He mumbled as he pulled the car out of the parking space. _Hilarious, you’re fucking lucky you have Cas._

Well, he wasn’t about to argue that.

When he sidled up to the space he had left Cas he immediately noticed two guys who were crowding in on Cas. Cas was pulling Dean’s jacket closer around himself, shaking his head as one of the guys were talking. The other guy even dared pull a little on Cas’ arm. Cas tried batting his hand away.

Dean was livid before he had even exited the car.

"Hey!" he roared over the pouring rain, stomping over to the three. "You get the fuck away from him."

"Him?" the guy pulling on Cas exclaimed in a squeaky voice.

"What the fuck, dude?" the other said in a disgusted voice and they both stepped back as if burned.

Dean reached Cas and pulled him close against his chest. "Fucking leave before I beat your face in."

"Jesus, calm the fuck down." The talker said but they were leaving before Dean could say anything more to them.

"Telling me to calm down." Dean muttered, hugging Cas closer. "Did they hurt you?"

Cas shook his head. When their eyes met Cas’ pupils looked blown. Dean sucked in a deep breath at the sight.

"I’m okay."

"I would’ve fucking beat them, Cas."

"I know."

Fuck, Cas was trembling but somehow Dean knew that it wasn’t from fear or cold. He put a hand on the small of Cas’ back and pulled him in so he could tilt Cas’ head up and kiss him demandingly. Cas melted against him.

"You’re mine, Cas." He growled. "No one can hurt you as long as I’m here."

"Dean." Cas gasped. "In the car."

Dean nodded harshly and bent down to retrieve the grocery bags. They got flung carelessly in the trunk as Cas climbed into the car.

Dean’s blood was rushing through his body, he felt high on adrenaline and endorphins. He needed and wanted and when Cas pointed to a seldom used gravel road he didn’t question it. Driving home would take too fucking long.

They wrestled themselves into the back seat, Cas crushed beneath Dean’s unforgiving weight and a moaning mess because of it. His legs were locked around Dean’s hips and they were rutting against each other in desperate motions.

"Need you, Dean."

"Gonna fuck you so good."

Lube and condoms were in the glove compartment because it had been ever since dad had first leant Dean this car. The car hadn’t seen even close to as much action as Dean would have liked, though, but that was good now, meant that there would be plenty left for them to use now.

"Give me one too." Cas said in a breathless tone and held out his hand for a condom. "Less mess."

Dean bit his lower lip to have some pain to focus on. He couldn’t fucking blow his load too soon this time, _needed_ to give Cas what he wanted. And if that was a desperate, hot fuck in the back of the Impala as the rain smattered down on the roof then that was what Dean was going to give him.

"Like this?" Dean asked and Cas nodded even as he pulled up his legs for easy access, his condom-clad dick pressed up against the bunched up skirt and his panties hanging off of one leg.

"Wanna see you."

"Fuck yeah."

Dean’s hands were shaking a little as he spread the lube on his fingers but he managed not to show it. He had watched _a lot_ of gay porn to be able to do this and he could fucking do it, damnit.

It wasn’t really that he thought he wouldn’t want to or something like that but the fact was that this was an exit hole. He was loath to hurt Cas just because he didn’t know what he was doing.

But Cas took one finger just beautifully, moaning and arching his back. His legs were pressed up and to the sides, his hands clenching the creaking leather seat.

"So fucking perfect." Dean breathed.

Cas’ dick jumped and his hole clenched around Dean. And yeah, Dean got the message loud and clear: hurry the fuck up.

Dean’s dick was on board with that.

Long (only felt long), hot moments passed, the only sounds the rain and their ragged breaths.

Then Dean found Cas’ prostate and Cas smacked his head on the door before Dean could catch him. Cas didn’t seem to mind, though, even if Dean’s heart lodged in his throat at the sight. The other boy was just moaning shamelessly, bucking up against Dean’s hand to get his finger back to that magic spot.

"Play with your nipples." Dean demanded in a reverent voice even as he inserted another finger.

Cas nodded and sat up a little to rip his shirt and padded bra over his head. It looked almost painful but he wrestled out of the clothes in no time, leaving Dean awed and _so fucking turned on_.

Cas rubbed his fingers over his perky nipples and was soon taking two of Dean’s thicker fingers. Scissoring, stretching. God, Cas’ body was tight and hot and Dean wanted _in_.

He had been fucking Cas on three fingers for only a few seconds before Cas keened desperately, making Dean weak with arousal. He gripped his own dick hard, squeezed once and was then ripping his jeans open.

"Need to be inside you now, baby. Please tell me you’re ready."

Cas nodded again, jerky motions that bumped his head against the door.

Dean ripped the condom packet with shaky hands, had to wipe his lube-slick fingers on his jeans before he managed. He gripped the back of the seat and hung his head for a moment as he rolled down the condom, his mouth open in an almost pleading moan.

"Oh Dean, need you." Cas’ little whimper brought him out of his haze. "Please take me, take me now."

"Always baby." He murmured soothingly before draping himself over Cas’ body, the blunt head of his dick against Cas’ quivering hole. "Want you so much."

They both groaned deeply when Dean pushed inside. And fucking hell it was tight. Like a goddamn vice and Dean couldn’t breathe properly. Cas was mewling again and bucking up against Dean but Dean had to take a fucking moment to collect himself or he would come just from this.

When they finally started moving in tandem it fucking blew his mind.

"G-God, Cas." He moaned loudly. His thrusts were powerful enough to shake the car. "You feel so good, I had no goddamn idea…"

"Faster, Dean, please…right there, oh!"

Dean bent down and captured Cas’ lips just as he managed to fuck right into the boy’s prostate. Cas thrashed against him, pulling, kissing, clenching. Dean put one hand behind Cas’ head to stop him from hitting it against the door. Squished his own fingers but fuck if he cared.

"Not gonna last at all, baby." Cas swallowed Dean’s hushed confession with a hungry kiss. "Wanted our first time to be proper, wanted to do you good."

"This is so good, so fucking good, Dean."

"You’re so pretty, deserve pretty."

Dean was incoherent, Cas even worse.

"Love this." Cas moaned. Dean’s throat felt tight with unexpected emotions. "Touch me Dean, oh please."

Dean was _never_ going to deny this beautiful wonder of a boy.

Cas came after only a short couple of hurried strokes and the way his inner walls rippled around Dean was much too much for Dean to handle.

He sobbed out his release into Cas’ greedy body, Cas kissing his face frantically, murmuring praise.

It was only after he had come down from his high that he noticed the rain still hammering down on the Impala’s roof. He had once again collapsed on top of Cas but this time he was also still lodged inside Cas and the boy’s dick was warm against Dean’s stomach even through his t-shirt.

Dean had never felt so whole.

  


*****

  


Gordon never came around but Dean didn’t mind. He had found new friends in Charlie and her geek squad and Benny and Garth stayed with Dean, much to Dean’s (secret) relief.

Fergus grumbled every time he saw Dean and Dean sneered right back. Cas rolled his eyes at their cock-measuring but the sex afterward was always amazing. Cas admitted to having a small fetish for Dean’s protectiveness and Dean was extremely willing to indulge him.

Sammy of course loved Cas, just like Dean had known he would. The two bonded over intellectual stuff that usually had Dean bored (when Sam was the one talking) but made him awed now (when Cas was the one talking). Sam teased him relentlessly for that.

Dad was confused for a long time and kept thinking that Dean was dating two people. One guy called Cas (which had been kind of a shock but he had rolled with it) and then this lovely girl (Cassie) that Dean brought around the house. He had actually cornered Dean just before the end of the school year (shortly after Dean and Cas had both gotten their acceptance letters to State University), telling Dean that he needed to man up and make a choice. That Cassie was too nice of a girl to be played with and that the boy Dean had on the side surely deserved better too. Needless to say Sam and Dean had laughed themselves breathless at that. Especially Dean could see the fun in it because of his own experience with the subject. Dad’s next meeting with "Cassie" had mostly consisted of him mumbling himself through an apology, red-faced with embarrassment while Cas had just looked confusedly at him.

It was still an enormous source of amusement for their whole family, years later. Dad grumbled every Christmas when Cas was goaded into telling the story over and over again (sometimes also adding the story of Dean’s own very similar mistake), much to the rest of the family’s delight. Dean always laughed the loudest while Cas smiled the brightest.

  
  


**Notes for the Chapter:**

> Until next time, lovelies <3


End file.
